Chemical and Pharmaceutical Bulletin
Online ISSN : 1347-5223
Print ISSN : 0009-2363
ISSN-L : 0009-2363
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Design, Synthesis and Biological Activity of Rigid Cannabinoid CB1 Receptor Antagonists
Axel Reinhard Stoit, Jos Hubertus Maria Lange, Arnold Peter den Hartog, Eric Ronken, Koos Tipker, Herman Heinrich van Stuivenberg, Jessica Adriana Rigtje Dijksman, Henri Cornelis Wals, Chris Gerrit Kruse
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Keywords: benzocycloheptapyrazole, CB1 receptor antagonist, molecular modeling, regiochemistry
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2002 Volume 50 Issue 8 Pages 1109-1113

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Abstract

The design, synthesis and biological activities of potent pyrazole-based tricyclic CB1 receptor antagonists (2) are described. The key synthetic step involves the ring closure of the lithiated α, γ-keto ester adduct (4). The optimal nitroderivative (28) in this series exhibits a high CB1 receptor affinity (pKi=7.2) as well as very potent antagonistic activity (pA2=8.8) in vitro. The regioselectivity of the pyrazole ring closure is shown to depend strongly on the aromatic substitution pattern of the applied arylhydrazine.

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© 2002 The Pharmaceutical Society of Japan
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